(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Base Information

• Chemical Name: (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine
• CAS No.: 1621585-09-8
• Molecular Formula: C₁₇H₁₇F₃N₄OS
• Molecular Weight: 382.409
• Mol file: 1621585-09-8.mol

Synonyms:(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Chemical Property of (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine

There total 15 articles about (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (1621585-57-6) → (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine (1621585-09-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 50 ℃; for 18h;

Reference yield:

2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine (1220328-95-9) → (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine (1621585-09-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium hypochlorite / water; dichloromethane / 1.5 h / 0 - 15 °C

2.1: boron trifluoride diethyl etherate / toluene; di-isopropyl ether / 0.5 h / -76 °C

2.2: 1.5 h / -76 - -71 °C

3.1: zinc; acetic acid / 16 h / 20 - 40 °C

4.1: dichloromethane / 18 h / 20 °C

5.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 3 h / -60 - -5 °C

6.1: boron trichloride / dichloromethane; n-heptane / 4.25 h / 0 - 20 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile; isopropyl alcohol / 3.5 h / 20 °C

8.1: acetic acid / tetrahydrofuran / 18 h / 20 °C

9.1: trifluoroacetic acid; pyridinium chlorochromate / acetonitrile / 3.5 h / 20 °C

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

11.1: bis(tri-n-butyltin); bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Inert atmosphere

12.1: trifluoroacetic acid; triethylsilane / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

13.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 18 h / 50 °C

With pyridine; triethylsilane; bis-triphenylphosphine-palladium(II) chloride; sodium hypochlorite; tetrapropylammonium perruthennate; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; bis(tri-n-butyltin); boron trichloride; potassium hexamethylsilazane; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; pyridinium chlorochromate; trifluoroacetic acid; zinc; In tetrahydrofuran; methanol; n-heptane; dichloromethane; di-isopropyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile;

Reference yield:

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(hydroxymethyl)-4,4-a,5,6,8,8a-hexahydropyrano[3,4-c][1,3]thiazin-2-yl]benzamide → (4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-amine (1621585-09-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine / dichloromethane / 0.08 h / 20 °C

1.2: 6.5 h / 20 °C

2.1: potassium carbonate / acetonitrile / 20.5 h / 20 °C / Inert atmosphere; Reflux

3.1: ruthenium trichloride; sodium periodate / water; acetonitrile; 1,2-dichloro-ethane / 21 h / 20 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1.43 h / -78 °C

5.1: bis(tri-n-butyltin); bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 120 °C / Inert atmosphere

6.1: trifluoroacetic acid; triethylsilane / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol / 18 h / 50 °C

With triethylsilane; ruthenium trichloride; bis-triphenylphosphine-palladium(II) chloride; sodium periodate; bis(tri-n-butyltin); potassium hexamethylsilazane; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

(4aR,6S,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-6-yl acetate

(4aR,8aS)-2-(benzoylamino)-8a-(2,4-difluorophenyl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-6-yl trifluoromethanesulfonate

N-[(4aR,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,8,8a-tetrahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

N-[(4aR,6R,8aS)-8a-(2,4-difluorophenyl)-6-(5-fluoro-1-methyl-1H-pyrazol-3-yl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide